Enantioselective Synthesis, Crystal Structure, and Photophysical Properties of a 1,1′-Bitriphenylene-Based Sila[7]helicene

Koichi Murayama; Yasuaki Oike; Seiichi Furumi; Masayuki Takeuchi; Keiichi Noguchi; Ken Tanaka

doi:10.1002/ejoc.201403565

Enantioselective Synthesis, Crystal Structure, and Photophysical Properties of a 1,1′-Bitriphenylene-Based Sila[7]helicene

Koichi Murayama, Yasuaki Oike, Seiichi Furumi, Masayuki Takeuchi, Keiichi Noguchi, Ken Tanaka

Research output: Contribution to journal › Article › peer-review

35 Citations (Scopus)

Abstract

A 1,1′-bitriphenylene-based sila[7]helicene was synthesized with a high ee value by enantioselective double [2+2+2] cycloaddition of a biaryl-linked tetrayne with a silicon-linked bis(propargylic alcohol) as a key step. This sila[7]helicene exhibited a high tolerance toward racemization, which could be explained by the X-ray crystal structure analysis. With respect to the photophysical properties, this sila[7]helicene exhibited a relatively high fluorescence quantum yield and circularly polarized luminescence activity.

Original language	English
Pages (from-to)	1409-1414
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	7
DOIs	https://doi.org/10.1002/ejoc.201403565
Publication status	Published - 2015 Mar
Externally published	Yes

Keywords

Cycloaddition
Helicenes
Luminescence
Rhodium
Triphenylenes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201403565

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Enantioselective Synthesis, Crystal Structure, and Photophysical Properties of a 1,1′-Bitriphenylene-Based Sila[7]helicene. / Murayama, Koichi; Oike, Yasuaki; Furumi, Seiichi; Takeuchi, Masayuki; Noguchi, Keiichi; Tanaka, Ken.

In: European Journal of Organic Chemistry, Vol. 2015, No. 7, 03.2015, p. 1409-1414.

Research output: Contribution to journal › Article › peer-review

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title = "Enantioselective Synthesis, Crystal Structure, and Photophysical Properties of a 1,1′-Bitriphenylene-Based Sila[7]helicene",

abstract = "A 1,1′-bitriphenylene-based sila[7]helicene was synthesized with a high ee value by enantioselective double [2+2+2] cycloaddition of a biaryl-linked tetrayne with a silicon-linked bis(propargylic alcohol) as a key step. This sila[7]helicene exhibited a high tolerance toward racemization, which could be explained by the X-ray crystal structure analysis. With respect to the photophysical properties, this sila[7]helicene exhibited a relatively high fluorescence quantum yield and circularly polarized luminescence activity.",

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author = "Koichi Murayama and Yasuaki Oike and Seiichi Furumi and Masayuki Takeuchi and Keiichi Noguchi and Ken Tanaka",

note = "Funding Information: This work was supported partly by ACT-C from Japan Science and Technology Agency (JST, Japan). We thank Nanotechnology Platform Project of MEXT, Japan. We also thank Mr. Yuta Miyauchi (TUAT) for his valuable assistance, Takasago International Corporation for the gift of Segphos, and Umicore for generous support in supplying the rhodium complex. Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Oike, Yasuaki

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AU - Takeuchi, Masayuki

AU - Noguchi, Keiichi

AU - Tanaka, Ken

N1 - Funding Information: This work was supported partly by ACT-C from Japan Science and Technology Agency (JST, Japan). We thank Nanotechnology Platform Project of MEXT, Japan. We also thank Mr. Yuta Miyauchi (TUAT) for his valuable assistance, Takasago International Corporation for the gift of Segphos, and Umicore for generous support in supplying the rhodium complex. Publisher Copyright: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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AB - A 1,1′-bitriphenylene-based sila[7]helicene was synthesized with a high ee value by enantioselective double [2+2+2] cycloaddition of a biaryl-linked tetrayne with a silicon-linked bis(propargylic alcohol) as a key step. This sila[7]helicene exhibited a high tolerance toward racemization, which could be explained by the X-ray crystal structure analysis. With respect to the photophysical properties, this sila[7]helicene exhibited a relatively high fluorescence quantum yield and circularly polarized luminescence activity.

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KW - Helicenes

KW - Luminescence

KW - Rhodium

KW - Triphenylenes

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Enantioselective Synthesis, Crystal Structure, and Photophysical Properties of a 1,1′-Bitriphenylene-Based Sila[7]helicene

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